Risque bet on the Super Bowl

[Daedalus]

A friend of mine and I have agreed to make some sort of bet on the Super Bowl, but we're struggling to find a suitable punishment for the loser. Something embarrassing, preferably, or challenging, and definitely risque if possible (nudity is pretty much assumed), but not too extreme. I live in San Francisco, FYI, if that helps with your suggestions. Also, risque probably doesn't mean anything outright sexual in this case.

Some issues we're facing....

1. I have roommates in a small place, so it would be really awkward to have him over to my place to administer the punishment. I'm pretty sure he's in a similar situation.

2. Neither one of us have a car, so we can't do some sort of driving around naked and jump out to do a dare. (I might consider signing up for Zipcar, though, if it seems required.)

3. Although public nudity is safer in SF than other cities, I'm just not comfortable walking around naked. I know too many people and it would be super awkward to run into someone I know. I could handle a quick streak in a remote area, but without a car, it would be hard to get to such a place.

4. We won't actually be watching the game together. The pay-up will occur at some other time to be determined later.


One idea would be for the loser to get spanked or paddled by the winner, a swat for every point difference between the winning and losing team. I hate pain, but this should be something that the loser doesn't want to do but is nevertheless willing to do. But...where?

Anyone have other ideas?

 

[denverbuttguy]

Something humiliating works. I've been on both sides of those bets and it was fun. I like going to a bathhouse and "paying off" the bet. That way there's always someone to watch. Make sure you let everyone know how it works out. I'll use it and make it a bet with my buddy for the next big event. Make it juicy!

 

[Daedalus]

Hmmm, a payoff in a sex club could be fun. Public without being too public.

 

[pieguy4ever]

work out details with the owner of a sex club or gay bar first, of course. with his consent, here's what you do:

both the winner and the loser walk in, both wearing the t-shirt of the winning team. the winner announces to whoever is there that you are going to strip down the other guy, who had the audicity to bet on the losing team. you get a crowd as you first take off his shoes, then his pants, then his socks, then his t-shirt, and finally his jock. so now he is naked.

you then announce that you two had the bet and the loser would be humiliated by guys at the club getting to schmush or splat pies in his face -- the number of pies based on the final point difference. if he loses by 10 points, then he gets 10 pies in the facel if he loses by 1 point, he just gets one pie. if he loses by 14, he gets 14. guys who want to pie a naked guy get a cream pie (can be as simple and cheap as shaving cream in a paper plate), one at a time, and let him have him right in the kisser.

this would be very humiliating, safe, fun, and sexy. maybe at the end the two of you kiss each other, so that the winner also gets creamed a little bit.

you would just have to provide a tarp (not expensive), several cans of shaving cream, some paper plates, and a few towels to clean up with afterwards.

whatcha think? my username tells you all you need to know about me ...

 

[otkboy]

Hi. This bet sounds very exciting and fun. Do tell us how it works out!

I absolutely love the spanking idea (spanking is perfect for this), but I suggest two additional ideas for you guys:

1. The winner shaves off all the loser's pubic hair (being completely shaved will be a nice humiliation for him in the gym showers)

2. The winner locks the loser in a chastity belt for a week

 

[Daedalus]

Hi. This bet sounds very exciting and fun. Do tell us how it works out!

I absolutely love the spanking idea (spanking is perfect for this), but I suggest two additional ideas for you guys:

1. The winner shaves off all the loser's pubic hair (being completely shaved will be a nice humiliation for him in the gym showers)

2. The winner locks the loser in a chastity belt for a week

Hmmm, good suggestions. I absolutely hate being spanked. Any sort of pain is a complete and total sexual turn-off for me. But I believe the loser should be willing to accept a risk for something he doesn't want to do, otherwise it's not really a risk. So I'll propose that as an option.

The shaving is a good idea. Since I don't belong to a gym, and I don't think he does, either, that limits the humiliation. But we can make it more embarrassing by arranging for it to be done semi-public like in a sex club.

Not sure about the chastity device, as he lives farther away and we rarely see each other more frequently than every six months.

 

[Storybook_Man]

A friend of mine and I have agreed to make some sort of bet on the Super Bowl, but we're struggling to find a suitable punishment for the loser. Something embarrassing, preferably, or challenging, and definitely risque if possible (nudity is pretty much assumed), but not too extreme. I live in San Francisco, FYI, if that helps with your suggestions. Also, risque probably doesn't mean anything outright sexual in this case.

Some issues we're facing....

1. I have roommates in a small place, so it would be really awkward to have him over to my place to administer the punishment. I'm pretty sure he's in a similar situation.

2. Neither one of us have a car, so we can't do some sort of driving around naked and jump out to do a dare. (I might consider signing up for Zipcar, though, if it seems required.)

3. Although public nudity is safer in SF than other cities, I'm just not comfortable walking around naked. I know too many people and it would be super awkward to run into someone I know. I could handle a quick streak in a remote area, but without a car, it would be hard to get to such a place.

4. We won't actually be watching the game together. The pay-up will occur at some other time to be determined later.


One idea would be for the loser to get spanked or paddled by the winner, a swat for every point difference between the winning and losing team. I hate pain, but this should be something that the loser doesn't want to do but is nevertheless willing to do. But...where?

Anyone have other ideas?

Well you said something embarrassing, seems like you don't want to be embarrassed, but embarrass him.. Suck it up and do it man! lol

 

[denverbuttguy]

Will you be together for the Super Bowl? You could have him send a picture or skype or just explain how it went if you weren't together--which ever of the two of you lost. You've got plenty of time before the Super Bowl. Great fun!

 

[Daedalus]

We won't be together for the Super Bowl, but we'll arrange for the penalty to be paid off at a later date when we can get together.

 

[Daedalus]

Okay, we finally came to agreement on a Super Bowl bet. He's less shy about public nudity than I am. If my team wins, he has to strip naked and take a walk with me anywhere I want to go. If I lose, my punishment will be more private -- I have to rent a private room for a few hours at one of those hot tub places, and he can do whatever he wants to me for a few hours.

 

[pieguy4ever]

and you view that as a 'penalty' for you if his team wins?

 

[Daedalus]

and you view that as a 'penalty' for you if his team wins?

Depends what he makes me do. He's into (or at least more experienced) some kinky stuff.

 

[gumshoe]

Sounds fun!

I liked the suggestions above about a bath house or whatever. I assume you're both gay? So that might not be a big deal.

Do let us know how it works out!

 

[palemale]

How about the loser has to have sex with whomever the winner picks off of a pick-up site and the winner gets to watch. The problem is, of course, that if you're a bottom and the winner picks a top with a 10" cock, you're in real trouble. haha.

 

[denverbuttguy]

I have a bet for the Super Bowl (thanks to replying to Daedalus' original post) and the loser does whatever the winner wants at the bath house. Not sure if I want to win or lose!

 

[Daedalus]

How about the loser has to have sex with whomever the winner picks off of a pick-up site and the winner gets to watch. The problem is, of course, that if you're a bottom and the winner picks a top with a 10" cock, you're in real trouble. haha.

I would be willing to do that, but the problem could be finding someone willing to have sex with me! I have, on different occasions as the result of losing stripping games, etc., had sex with (1) someone who was around 400 pounds, (2) someone who was around 60 and gave great head, and (3) someone who was over 80. For a bet, I'd be willing to engage sexually with someone I was totally not attracted to, even a girl -- but in that case, only if a straight guy was willing to risk have sex with another guy.

 

[Daedalus]

Glad to see others are taking up the idea and placing their own Super Bowl bets. I'd propose a JUBber where losers have to post pics of themselves performing the required penalty, but I don't have the guts to post pics of myself.

 

[palemale]

I would be willing to do that, but the problem could be finding someone willing to have sex with me! I have, on different occasions as the result of losing stripping games, etc., had sex with (1) someone who was around 400 pounds, (2) someone who was around 60 and gave great head, and (3) someone who was over 80. For a bet, I'd be willing to engage sexually with someone I was totally not attracted to, even a girl -- but in that case, only if a straight guy was willing to risk have sex with another guy.

Sex with someone over 400lbs???? Holy shit, what did you do with him? Also, why do you think it would be a problem finding someone to have sex with you?